2-Fluorobenzoyl chloride → HCID 67153831, compound

HRID 714331Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][N:37]=1)[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>>[CH2:28]([NH:27][C:25](=[O:26])[C:24]1[CH:35]=[CH:36][N:37]=[C:22]([NH:21][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:12]([F:11])=[CH:13][CH:14]=2)[CH:23]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 678794-Fluorobenzoyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153831HCID 67153831, compoundYield 27%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 4-fluorobenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-fluorobenzamido)isonicotinamide was obtained as a colorless solid in 27% yield: mp 170-171° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.70 (s, 1H), 8.70 (s, 1H), 8.40 (d, J=5.1 Hz, 1H), 7.95-7.88 (m, 2H), 7.57 (dd, J=5.7, 1.5 Hz, 1H), 7.37-7.26 (m, 5H), 7.20-7.14 (m, 2H), 6.78-6.65 (m, 1H), 4.64 (d, J=5.8 Hz, 2H); MS (ES+) m/z 350.5 (M+1).

Sources & evidence

ORD record: ord-fd2745af4c9a41d2bf0cf78c197231c9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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